CA1206472A - Anthracyclinone glycosides and their preparation method - Google Patents

Anthracyclinone glycosides and their preparation method

Info

Publication number: CA1206472A
Authority: CA; Canada
Prior art keywords: hydrogen; formula; glycoside; acid addition; acceptable acid
Prior art date: 1981-04-23
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired

Application number

CA000401265A

Other languages

English (en)

French (fr)

Inventor

Hamao Umezawa

Tomio Takeuchi

Hiroshi Tanaka

Toshikazu Oki

Tomoyuki Ishikura

Yasutaka Shimauchi

Takeo Yoshioka

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Sanraku Ocean Co Ltd

Original Assignee

Sanraku Ocean Co Ltd

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1981-04-23

Filing date

1982-04-20

Publication date

1986-06-24

1982-04-20 Application filed by Sanraku Ocean Co Ltd filed Critical Sanraku Ocean Co Ltd

1986-06-24 Application granted granted Critical

1986-06-24 Publication of CA1206472A publication Critical patent/CA1206472A/en

Status Expired legal-status Critical Current

Links

229930182470 glycoside Natural products 0.000 title claims abstract description 111
150000002338 glycosides Chemical class 0.000 title claims abstract description 108
238000002360 preparation method Methods 0.000 title claims abstract description 32
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 229
239000001257 hydrogen Substances 0.000 claims abstract description 227
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 173
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 53
239000000126 substance Substances 0.000 claims abstract description 41
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 33
239000002253 acid Substances 0.000 claims description 75
238000007792 addition Methods 0.000 claims description 73
150000003839 salts Chemical class 0.000 claims description 70
150000002431 hydrogen Chemical group 0.000 claims description 61
238000000034 method Methods 0.000 claims description 55
150000001875 compounds Chemical class 0.000 claims description 48
-1 amino, monomethylamino Chemical group 0.000 claims description 46
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 39
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 39
125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 32
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 31
125000000217 alkyl group Chemical group 0.000 claims description 27
125000003710 aryl alkyl group Chemical group 0.000 claims description 26
125000004430 oxygen atom Chemical group O* 0.000 claims description 20
238000005858 glycosidation reaction Methods 0.000 claims description 16
235000000346 sugar Nutrition 0.000 claims description 15
238000005904 alkaline hydrolysis reaction Methods 0.000 claims description 9
239000003960 organic solvent Substances 0.000 claims description 9
JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 9
238000007069 methylation reaction Methods 0.000 claims description 5
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 4
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 3
239000007795 chemical reaction product Substances 0.000 claims description 3
125000005207 tetraalkylammonium group Chemical group 0.000 claims description 2
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 12
239000001301 oxygen Substances 0.000 claims 12
229910052760 oxygen Inorganic materials 0.000 claims 12
239000007858 starting material Substances 0.000 claims 11
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 8
DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Chemical group CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims 3
150000001241 acetals Chemical group 0.000 claims 3
LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims 1
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 80
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 69
229960001701 chloroform Drugs 0.000 description 35
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 33
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 33
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 32
239000000243 solution Substances 0.000 description 26
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 21
235000013350 formula milk Nutrition 0.000 description 19
AOJJSUZBOXZQNB-TZSSRYMLSA-N Doxorubicin Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(=O)CO)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 AOJJSUZBOXZQNB-TZSSRYMLSA-N 0.000 description 18
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
YOFDHOWPGULAQF-UHFFFAOYSA-N Daunomycin-Aglycone Natural products C1C(O)(C(C)=O)CC(O)C2=C1C(O)=C1C(=O)C(C=CC=C3OC)=C3C(=O)C1=C2O YOFDHOWPGULAQF-UHFFFAOYSA-N 0.000 description 15
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 15
239000000843 powder Substances 0.000 description 15
238000001704 evaporation Methods 0.000 description 14
230000008020 evaporation Effects 0.000 description 14
238000002844 melting Methods 0.000 description 14
230000008018 melting Effects 0.000 description 14
239000011541 reaction mixture Substances 0.000 description 14
IBZGBXXTIGCACK-CWKPULSASA-N Adriamycinone Chemical compound C1[C@@](O)(C(=O)CO)C[C@H](O)C2=C1C(O)=C1C(=O)C(C=CC=C3OC)=C3C(=O)C1=C2O IBZGBXXTIGCACK-CWKPULSASA-N 0.000 description 13
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 11
229940022682 acetone Drugs 0.000 description 11
239000000203 mixture Substances 0.000 description 11
229910000402 monopotassium phosphate Inorganic materials 0.000 description 11
235000019796 monopotassium phosphate Nutrition 0.000 description 11
GNSKLFRGEWLPPA-UHFFFAOYSA-M potassium dihydrogen phosphate Chemical compound [K+].OP(O)([O-])=O GNSKLFRGEWLPPA-UHFFFAOYSA-M 0.000 description 11
LWIHDJKSTIGBAC-UHFFFAOYSA-K potassium phosphate Substances [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 11
239000000741 silica gel Substances 0.000 description 11
229910002027 silica gel Inorganic materials 0.000 description 11
239000002904 solvent Substances 0.000 description 11
YOFDHOWPGULAQF-MQJDWESPSA-N (7s,9s)-9-acetyl-6,7,9,11-tetrahydroxy-4-methoxy-8,10-dihydro-7h-tetracene-5,12-dione Chemical compound C1[C@@](O)(C(C)=O)C[C@H](O)C2=C1C(O)=C1C(=O)C(C=CC=C3OC)=C3C(=O)C1=C2O YOFDHOWPGULAQF-MQJDWESPSA-N 0.000 description 10
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 10
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 10
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 9
MDUVOMDREZPQPI-UHFFFAOYSA-N Aklavinone Natural products CCC1(O)CC(O)c2c(O)c3C(=O)C4C(C=CC=C4O)C(=O)c3cc2C1C(=O)OC MDUVOMDREZPQPI-UHFFFAOYSA-N 0.000 description 9
229940009456 adriamycin Drugs 0.000 description 9
RACGRCLGVYXIAO-YOKWENHESA-N aklavinone Chemical compound O=C1C2=C(O)C=CC=C2C(=O)C2=C1C(O)=C1[C@@H](O)C[C@@](CC)(O)[C@H](C(=O)OC)C1=C2 RACGRCLGVYXIAO-YOKWENHESA-N 0.000 description 9
230000000259 anti-tumor effect Effects 0.000 description 9
238000002474 experimental method Methods 0.000 description 9
BWZVCCNYKMEVEX-UHFFFAOYSA-N 2,4,6-Trimethylpyridine Chemical compound CC1=CC(C)=NC(C)=C1 BWZVCCNYKMEVEX-UHFFFAOYSA-N 0.000 description 8
STQGQHZAVUOBTE-UHFFFAOYSA-N 7-Cyan-hept-2t-en-4,6-diinsaeure Natural products C1=2C(O)=C3C(=O)C=4C(OC)=CC=CC=4C(=O)C3=C(O)C=2CC(O)(C(C)=O)CC1OC1CC(N)C(O)C(C)O1 STQGQHZAVUOBTE-UHFFFAOYSA-N 0.000 description 8
WEAHRLBPCANXCN-UHFFFAOYSA-N Daunomycin Natural products CCC1(O)CC(OC2CC(N)C(O)C(C)O2)c3cc4C(=O)c5c(OC)cccc5C(=O)c4c(O)c3C1 WEAHRLBPCANXCN-UHFFFAOYSA-N 0.000 description 8
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
STQGQHZAVUOBTE-VGBVRHCVSA-N daunorubicin Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(C)=O)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 STQGQHZAVUOBTE-VGBVRHCVSA-N 0.000 description 8
239000007924 injection Substances 0.000 description 8
229940090044 injection Drugs 0.000 description 8
238000002347 injection Methods 0.000 description 8
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 8
239000000725 suspension Substances 0.000 description 8
XYDJGVROLWFENK-YBTHPKLGSA-N (7s,9s)-9-acetyl-4,6,7,9,11-pentahydroxy-8,10-dihydro-7h-tetracene-5,12-dione Chemical compound O=C1C2=C(O)C=CC=C2C(=O)C2=C1C(O)=C1[C@@H](O)C[C@@](C(=O)C)(O)CC1=C2O XYDJGVROLWFENK-YBTHPKLGSA-N 0.000 description 7
229960004176 aclarubicin Drugs 0.000 description 7
238000006243 chemical reaction Methods 0.000 description 7
239000000706 filtrate Substances 0.000 description 7
229910000030 sodium bicarbonate Inorganic materials 0.000 description 7
235000017557 sodium bicarbonate Nutrition 0.000 description 7
229960001407 sodium bicarbonate Drugs 0.000 description 7
150000004043 trisaccharides Chemical class 0.000 description 7
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
239000002026 chloroform extract Substances 0.000 description 6
239000003480 eluent Substances 0.000 description 6
238000001914 filtration Methods 0.000 description 6
239000000047 product Substances 0.000 description 6
238000010898 silica gel chromatography Methods 0.000 description 6
PITHJRRCEANNKJ-UHFFFAOYSA-N Aclacinomycin A Natural products C12=C(O)C=3C(=O)C4=CC=CC=C4C(=O)C=3C=C2C(C(=O)OC)C(CC)(O)CC1OC(OC1C)CC(N(C)C)C1OC(OC1C)CC(O)C1OC1CCC(=O)C(C)O1 PITHJRRCEANNKJ-UHFFFAOYSA-N 0.000 description 5
TWCMVXMQHSVIOJ-UHFFFAOYSA-N Aglycone of yadanzioside D Natural products COC(=O)C12OCC34C(CC5C(=CC(O)C(O)C5(C)C3C(O)C1O)C)OC(=O)C(OC(=O)C)C24 TWCMVXMQHSVIOJ-UHFFFAOYSA-N 0.000 description 5
PLMKQQMDOMTZGG-UHFFFAOYSA-N Astrantiagenin E-methylester Natural products CC12CCC(O)C(C)(CO)C1CCC1(C)C2CC=C2C3CC(C)(C)CCC3(C(=O)OC)CCC21C PLMKQQMDOMTZGG-UHFFFAOYSA-N 0.000 description 5
101150041968 CDC13 gene Proteins 0.000 description 5
241000699670 Mus sp. Species 0.000 description 5
USZYSDMBJDPRIF-SVEJIMAYSA-N aclacinomycin A Chemical compound O([C@H]1[C@@H](O)C[C@@H](O[C@H]1C)O[C@H]1[C@H](C[C@@H](O[C@H]1C)O[C@H]1C[C@]([C@@H](C2=CC=3C(=O)C4=CC=CC(O)=C4C(=O)C=3C(O)=C21)C(=O)OC)(O)CC)N(C)C)[C@H]1CCC(=O)[C@H](C)O1 USZYSDMBJDPRIF-SVEJIMAYSA-N 0.000 description 5
238000000434 field desorption mass spectrometry Methods 0.000 description 5
PFOARMALXZGCHY-UHFFFAOYSA-N homoegonol Natural products C1=C(OC)C(OC)=CC=C1C1=CC2=CC(CCCO)=CC(OC)=C2O1 PFOARMALXZGCHY-UHFFFAOYSA-N 0.000 description 5
239000002808 molecular sieve Substances 0.000 description 5
229910052757 nitrogen Inorganic materials 0.000 description 5
229910000027 potassium carbonate Inorganic materials 0.000 description 5
URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 5
JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 5
238000004809 thin layer chromatography Methods 0.000 description 5
AUHZEENZYGFFBQ-UHFFFAOYSA-N 1,3,5-Me3C6H3 Natural products CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 4
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UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 4
238000013019 agitation Methods 0.000 description 4
239000003242 anti bacterial agent Substances 0.000 description 4
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239000007864 aqueous solution Substances 0.000 description 4
230000015572 biosynthetic process Effects 0.000 description 4
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GFYHSKONPJXCDE-UHFFFAOYSA-N sym-collidine Natural products CC1=CN=C(C)C(C)=C1 GFYHSKONPJXCDE-UHFFFAOYSA-N 0.000 description 4
238000003786 synthesis reaction Methods 0.000 description 4
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
WJKHJLXJJJATHN-UHFFFAOYSA-N triflic anhydride Chemical compound FC(F)(F)S(=O)(=O)OS(=O)(=O)C(F)(F)F WJKHJLXJJJATHN-UHFFFAOYSA-N 0.000 description 4
OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 3
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239000003054 catalyst Substances 0.000 description 3
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
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WMUYJHSRMOORHK-BIIVOSGPSA-N C[C@H](O)[C@@H](O)[C@@H](N(C)C)CC=O Chemical compound C[C@H](O)[C@@H](O)[C@@H](N(C)C)CC=O WMUYJHSRMOORHK-BIIVOSGPSA-N 0.000 description 2
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VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
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WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
COVZYZSDYWQREU-UHFFFAOYSA-N Busulfan Chemical compound CS(=O)(=O)OCCCCOS(C)(=O)=O COVZYZSDYWQREU-UHFFFAOYSA-N 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
GHOKWGTUZJEAQD-UHFFFAOYSA-N Chick antidermatitis factor Natural products OCC(C)(C)C(O)C(=O)NCCC(O)=O GHOKWGTUZJEAQD-UHFFFAOYSA-N 0.000 description 1
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
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WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 description 1
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
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KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
230000021736 acetylation Effects 0.000 description 1
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238000005903 acid hydrolysis reaction Methods 0.000 description 1
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230000002378 acidificating effect Effects 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
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238000010171 animal model Methods 0.000 description 1
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238000013459 approach Methods 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
229940076134 benzene Drugs 0.000 description 1
230000003115 biocidal effect Effects 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
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KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
150000001720 carbohydrates Chemical class 0.000 description 1
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125000004432 carbon atom Chemical group C* 0.000 description 1
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230000001451 cardiotoxic effect Effects 0.000 description 1
230000010261 cell growth Effects 0.000 description 1
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235000015165 citric acid Nutrition 0.000 description 1
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230000009089 cytolysis Effects 0.000 description 1
230000017858 demethylation Effects 0.000 description 1
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150000002016 disaccharides Chemical class 0.000 description 1
230000003203 everyday effect Effects 0.000 description 1
235000019253 formic acid Nutrition 0.000 description 1
239000001530 fumaric acid Substances 0.000 description 1
235000011087 fumaric acid Nutrition 0.000 description 1
239000011521 glass Substances 0.000 description 1
239000004220 glutamic acid Substances 0.000 description 1
235000013922 glutamic acid Nutrition 0.000 description 1
230000026030 halogenation Effects 0.000 description 1
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230000003301 hydrolyzing effect Effects 0.000 description 1
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QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
231100001231 less toxic Toxicity 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
239000011976 maleic acid Substances 0.000 description 1
238000005259 measurement Methods 0.000 description 1
IZDROVVXIHRYMH-UHFFFAOYSA-N methanesulfonic anhydride Chemical compound CS(=O)(=O)OS(C)(=O)=O IZDROVVXIHRYMH-UHFFFAOYSA-N 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
230000004048 modification Effects 0.000 description 1
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150000007523 nucleic acids Chemical class 0.000 description 1
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MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 1
239000011713 pantothenic acid Substances 0.000 description 1
229940055726 pantothenic acid Drugs 0.000 description 1
235000019161 pantothenic acid Nutrition 0.000 description 1
229910052698 phosphorus Inorganic materials 0.000 description 1
229910003446 platinum oxide Inorganic materials 0.000 description 1
230000003389 potentiating effect Effects 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
235000019260 propionic acid Nutrition 0.000 description 1
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
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238000000926 separation method Methods 0.000 description 1
229940006198 sodium phenylacetate Drugs 0.000 description 1
238000000638 solvent extraction Methods 0.000 description 1
150000008163 sugars Chemical class 0.000 description 1
230000006103 sulfonylation Effects 0.000 description 1
238000005694 sulfonylation reaction Methods 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
DKVBOUDTNWVDEP-NJCHZNEYSA-N teicoplanin aglycone Chemical compound N([C@H](C(N[C@@H](C1=CC(O)=CC(O)=C1C=1C(O)=CC=C2C=1)C(O)=O)=O)[C@H](O)C1=CC=C(C(=C1)Cl)OC=1C=C3C=C(C=1O)OC1=CC=C(C=C1Cl)C[C@H](C(=O)N1)NC([C@H](N)C=4C=C(O5)C(O)=CC=4)=O)C(=O)[C@@H]2NC(=O)[C@@H]3NC(=O)[C@@H]1C1=CC5=CC(O)=C1 DKVBOUDTNWVDEP-NJCHZNEYSA-N 0.000 description 1
238000002054 transplantation Methods 0.000 description 1
YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
238000010792 warming Methods 0.000 description 1
150000008135 α-glycosides Chemical class 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/20—Carbocyclic rings
- C07H15/24—Condensed ring systems having three or more rings
- C07H15/252—Naphthacene radicals, e.g. daunomycins, adriamycins
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
General Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Biochemistry (AREA)
Biotechnology (AREA)
Genetics & Genomics (AREA)
Molecular Biology (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Pharmacology & Pharmacy (AREA)
Animal Behavior & Ethology (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Saccharide Compounds (AREA)

CA000401265A 1981-04-23 1982-04-20 Anthracyclinone glycosides and their preparation method Expired CA1206472A (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
JP56-61766		1981-04-23
JP56061766A JPS57176995A (en)	1981-04-23	1981-04-23	Novel anthracyclinone glycoside and its preparation

Publications (1)

Publication Number	Publication Date
CA1206472A true CA1206472A (en)	1986-06-24

Family

ID=13180567

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000401265A Expired CA1206472A (en)	1981-04-23	1982-04-20	Anthracyclinone glycosides and their preparation method

Country Status (5)

Country	Link
US (1)	US4418192A (de)
EP (1)	EP0063776B1 (de)
JP (1)	JPS57176995A (de)
CA (1)	CA1206472A (de)
DE (1)	DE3266311D1 (de)

Families Citing this family (12)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS5874694A (ja) *	1981-10-29	1983-05-06	Sanraku Inc	アントラサイクリン誘導体
JPS5982395A (ja) *	1982-11-02	1984-05-12	Microbial Chem Res Found	アントラサイクリン化合物、その製造法およびその用途
DE3323025A1 (de) *	1983-06-25	1985-01-10	Hoechst Ag, 6230 Frankfurt	Anthracyclin-derivate, ein mikrobiologisches verfahren zu ihrer herstellung und ihre verwendung als cytostatika
FR2551057B1 (fr) *	1983-08-30	1986-07-18	Hoechst Lab	Nouveaux aglycones utiles pour la preparation des antibiotiques et des antitumoraux de la serie des anthracyclines et leurs procedes de preparation
DE3524117A1 (de) *	1985-07-05	1987-02-05	Hoechst Ag	Neue anthracyclin-tetrasaccharide, ein verfahren zu ihrer herstellung und ihre verwendung als cytostatik
DE3641833A1 (de) *	1986-12-08	1988-06-09	Behringwerke Ag	Zytostatisch wirksame anthracyclinderivate
DE3706175A1 (de) *	1987-02-26	1988-09-08	Behringwerke Ag	Verwendung von lipophilen anthracyclinen zur behandlung "sekundaer" anthracyclin-resistenter tumoren, mittel enthaltend ein lipophiles anthracyclin und verfahren zu seiner herstellung
US4918172A (en) *	1987-10-06	1990-04-17	Sanraku Incorporated	Anthracycline antibiotics
DE3819092A1 (de) *	1988-06-04	1989-12-14	Behringwerke Ag	Zytostatisch wirksame anthracyclinderivate
JPH0679039U (ja) *	1993-04-06	1994-11-04	日本コロムビア株式会社	回転ノブ
IT1282379B1 (it) *	1996-04-24	1998-03-20	Mini Ricerca Scient Tecnolog	Disaccaridi di antracicline antitumorali.
WO2012082635A1 (en) *	2010-12-13	2012-06-21	Ancora Pharmaceuticals, Inc.	Synthetic oligosaccharide group a streptococcus

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* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3772269A (en) *	1969-07-24	1973-11-13	Ici America Inc	Glycoside compositions and process for the preparation thereof
US4039663A (en) *	1975-03-19	1977-08-02	Societa' Farmaceutici Italia S.P.A.	Daunomycins, process for their uses and intermediates
GB1561507A (en) *	1976-11-17	1980-02-20	Farmaceutici Italia	Snthracycline disaccharides
US4216208A (en) *	1978-07-31	1980-08-05	Proter S.P.A.	N-Acyl derivatives of glucosamines having antitumor chemotherapeutic activity
JPS55104225A (en) *	1979-02-06	1980-08-09	Sanraku Inc	Anthracyclines and their preparation
JPS55108889A (en) *	1979-02-15	1980-08-21	Sanraku Inc	4-o-methylaclacinomycin a and its preparation
ZA802929B (en) *	1979-05-22	1981-05-27	Hoffmann La Roche	Novel tetracyclic compounds and process for the preparation thereof
JPS6023679B2 (ja) *	1979-07-13	1985-06-08	メルシャン株式会社	ロドマイシン群抗生物質とその製造法
US4318790A (en) *	1980-03-17	1982-03-09	The Upjohn Company	Photochemical process for preparing N-demethyl-derivatives of nogalamycin

1981
- 1981-04-23 JP JP56061766A patent/JPS57176995A/ja active Pending
1982
- 1982-04-20 US US06/370,212 patent/US4418192A/en not_active Expired - Fee Related
- 1982-04-20 DE DE8282103319T patent/DE3266311D1/de not_active Expired
- 1982-04-20 CA CA000401265A patent/CA1206472A/en not_active Expired
- 1982-04-20 EP EP82103319A patent/EP0063776B1/de not_active Expired

Also Published As

Publication number	Publication date
DE3266311D1 (en)	1985-10-24
JPS57176995A (en)	1982-10-30
EP0063776B1 (de)	1985-09-18
EP0063776A1 (de)	1982-11-03
US4418192A (en)	1983-11-29

Legal Events

Date	Code	Title	Description
2003-06-24	MKEX	Expiry

Publication	Publication Date	Title
HRP920898A2 (en)	1997-04-30	4-demethoxy-4-amino-anthracyclines and a process for the preparation thereof
EP0063776B1 (de)	1985-09-18	Anthracyclinon-Glycoside und Verfahren zu deren Herstellung
US4366149A (en)	1982-12-28	Antitumor anthracycline glycosides, their preparation, intermediates therefor, and compositions and use thereof
NZ208622A (en)	1988-02-29	Anthracycline derivatives, preparation by fermentation process and pharmaceutical compositions
Matsuzawa et al.	1981	New anthracycline metabolites from mutant strains of Streptomyces galilaeus MA144-M1 II. Structure of 2-hydroxyaklavinone and new aklavinone glycosides
US4325946A (en)	1982-04-20	Anthracycline glycosides, their preparation, use and compositions thereof
US4303785A (en)	1981-12-01	Antitumor anthracycline antibiotics
CA1090788A (en)	1980-12-02	Process for the preparation of antitumor glycosides
HÜTTER et al.	1986	Viriplanin A, a new anthracycline antibiotic of the nogalamycin group I. Isolation, characterization, degradation reactions and biological properties
JOHDO et al.	1991	ANTHRACYCLINE METABOLITES FROM Streptomyces violaceous A262 II. NEW ANTHRACYCLINE EPELMYCINS PRODUCED BY A BLOCKED MUTANT STRAIN SU2-730
US4322412A (en)	1982-03-30	Anthracycline glycosides, their preparation, use and compositions thereof
CA1128503A (en)	1982-07-27	Process for the preparation of substituted antitumor anthracyclines
EP0014425B1 (de)	1982-06-02	Anthracyclinglycosiden, Verfahren zu deren Herstellung und sie enthaltende therapeutische Zusammensetzungen
US4612371A (en)	1986-09-16	Anthracycline antibiotics
US4265885A (en)	1981-05-05	Anthracyclines containing branched-chain amino-deoxy sugars
EP1140962B1 (de)	2007-02-21	Oleandomycin-derivate
YOSHIMOTO et al.	1992	Anthracycline metabolites from baumycin-producing Streptomyces sp. D788 I. Isolation of antibiotic-blocked mutants and their characterization
JOHDO et al.	1991	ANTHRACYCLINE METABOLITES FROM Streptomyces violaceus A262 III. NEW ANTHRACYCLINE OBELMYCINS PRODUCED BY A VARIANT STRAIN SE2-2385
JPH0778073B2 (ja)	1995-08-23	ニトロアントラサイクリン、その製造方法およびその使用
US4501699A (en)	1985-02-26	Maggiemycin, anhydromaggiemycin and processes for making
EP0683787B1 (de)	1997-09-10	4'-0-sulfonylanthracyclinderivate
JOHDO et al.	1992	Production of new anthracycline antibiotics by microbial 4-O-methylation using a specific daunorubicin-negative mutant
Yoshimoto et al.	1992	Production of new anthracycline antibiotic betaclamycin B by microbial conversion with a specific aclacinomycin-negative mutant
CA2056823C (en)	1999-04-27	Derivatives of 10,11,12,13-tetrahydrodesmycosin processes for preparation, and use thereof in pharmaceuticals
EP0167935B1 (de)	1989-08-30	Anthracyclinderivate, deren Verfahren zur Herstellung und deren pharmazeutische Zusammensetzung und deren Benützung als Arznei